PROBLEM

4. Which alkyl halide would you expect to be more reactive (faster) in and SN2 reaction with a given
nucleophile? (explain your answers)
a. Bromopropane or iodopropane
b. 2-bromobutane or 3-bromopentane
c. 2-bromopentane or 1-bromo-2-methylbutane
d. 2-bromoethylbenzene or 2-bromopropylbenzene
e. Bromomethylbenzene or bromobenzene
Which alkyl halide would you expect to be more reactive (faster) in and SN1 reaction with a given
nucleophile? (explain your answers)
a. Bromopropane or iodopropane
b. 2-bromobutane or 3-bromopentane
c. 2-bromopentane or 1-bromo-2-methylbutane
d. 2-bromoethylbenzene or 2-bromopropylbenzene
e. Bromomethylbenzene or bromobenzene
f. 2-bromo-2-pentene or 4-bromo-2-pentene

ANSWER
The order for alkyl halides towards SN2 are: primary > secondary > tertiary

This is because the stearic hindrence near leaving group increases from primary to tertialy halide.
Additionally, better leaving groups present at alkyl halide increases the rate of SN2 reaction.

The order for alkyl halides towards SN1 are: primary < secondary < tertiary

This is because the stability of carbocation formed after realease of leaving group increases in the
same order. any factor which stabilize the carbocation would favour SN1 reaction. Additionally, in
this case also better leaving groups present at alkyl halide increases the rate of SN1 reaction.

First draw all the structures of given compounds and then observe for all these factors and get the
conclusion.